The smart way to take risks

You have to juggle chance and caution to get anywhere.

Photo by Stephany Lorena on Unsplash

Uncertainty can paralyze anyone. You don’t always know what to do. Or what’s going to happen. That’s why most of us don’t like taking chances. We don’t want to screw up what we’ve got.

Maybe you’re thinking about quitting your job. Or killing a perfectly good relationship. They don’t make you happy anymore.

But you start to worry. That you’ll wind up alone. Unemployed. You’ll change your mind. After it’s too late.

Now you’re fucked. Life ruined. Game over.

Some people flaunt their risk. They love bragging about how they ditched a boring job to launch their startup. No plan yet. But they’re committed. A hundred percent.

Walk into any coffee shop, and you’ll spot at least one entrepreneur, aka someone who only takes risks while posing with a mocha.

Heads up. Risk has a long history. There’s even a board game named after it. We all take risks. We analyze. Speculate. Make a mistake. Find out the mistake wasn’t a mistake after all.

That happened to me a few years ago. The guy I was dating was attractive. Reasonably smart. We got along well. Most of the time.

But he was also immature. Jealous. Insecure — intellectually and emotionally. He threw little tantrums anytime I spent 30 seconds talking to a member of the opposite sex. Threatened to dump me over board games — like Risk. Flirted with girls to distract me from his own envy.

After a year, I met someone else and had to make a tough call. Keep the relationship I had. Or take a chance. In the end, I took the chance and wound up single. But happier.

That’s the thing about chance. If you take one, you have to live with the consequences. People forget what real chance involves. You always give up something. Nobody takes a chance and goes unscathed.

The smart way to take chances

A toxic version of risk has always lurked through pop culture. Quit your job to pursue your passion. Sell your stuff and travel the world. Dump your boyfriend and jump on a plane somewhere. Anywhere.

Do something spontaneous. Anything. Move to Australia. Fake a seizure in a Starbucks. Why? I don’t know. Maybe you’ll go viral.

Not every risk means quitting your job. It’s just the most dramatic. Looks great in movies. Especially if you storm out. Or pull a Jerry Maguire.

Sometimes I want to write a midnight manifesto and send it to everyone at my university. But I don’t. That would be stupid. Other ways exist for me to reform practices at my school.

Posting a diatribe to the faculty list-serve would make for a great opening scene in a Netflix Original. Probably get me fired.

Not a smart risk. On the other hand, blogging under a pseudonym also poses a risk to me. One I’m willing to accept.

Not everyone who goes viral makes a million dollars. You could spend your life taking “chances” and posting the results on YouTube.

If you feel like doing that, great.

Spontaneity doesn’t always make you happy, or rich. Don’t take risks for their own sake. Chance always needs purpose and conviction. Travel the world because you feel compelled to. Not because you feel the need to take more risks and break your comfort zone.

This one friend of mine has made a life out of risks. Quit her boring newspaper job to freelance. Traveled the world. Still lives from paycheck to paycheck. Hey, she tells great stories. But I’ve never wanted to live like that. I’ve always wanted at least some degree of stability.

Risk comes in all kinds of shapes. For me, going for a PhD posed a lot of risk. My parents thought I was throwing my life away. So did some of my friends. Teachers don’t make much money.

Taking a chance doesn’t mean you shouldn’t have a backup plan. So you want to become a painter. Great. You can learn how to use design software, too. Just in case. That’s not defeatism. That’s brains.

My whole life feels like a risk. I knew up front I’d rather fail at the thing I wanted than take the safer course and major in business administration and tourism. That kind of shit leads to a midlife crisis. But I’ve always worked on backup plans. In fact, my backup plans turned into dreams.

When you don’t take risks

My ex-fiance played it safe. His parents raised him that way. Back in high school they wouldn’t even let him drive on the highway. When he finished college, they forced him to quit his job at a major nonprofit publisher and go to law school instead.

I’m using the word “forced” loosely here. After 18, your parents can’t force you to do much anymore. He was just so desperate for their approval, they could use it against him. Poor guy.

His life showed me what it looks like to truly avoid risk. He hated law school. It caused him to lose weight. He developed an ulcer. Started having panic attacks. But he kept on, all to avoid confrontation.

Meanwhile, the parents grew increasingly judgmental of me. The free spirit. The bitch who was working on an MFA. What’s she going to do with that? Become some famous writer? Laugh.

We broke up his second year of law school. Partly because the stress was driving him mental. But mainly because he didn’t believe in me. Or my love. He dumped me out of fear.

Risk has never been a difficult thing for me. I’m not sure why. If I want to do something, I’ll do it. Fuck the consequences. Rock climbing. Not always in legally-zoned areas, or with the proper equipment. Trespassing into abandoned buildings. Even if I get arrested. One night stands. Whatever feels right but also not suicidal.

It’s fine to pass up chances if you don’t feel compelled. I’ll probably never go sky-diving, but tornado hunting’s on my bucket list. Passing up opportunities out of fear, though. That kills you a little.

You already know what to do

A lot of people wallow in uncertainty just to avoid pain. You’ve already made up your mind. But you don’t want to follow through. Somehow, the space between two possible lives feels safe.

The safe feeling comes at a price. I’ve never enjoyed uncertainty. I’d rather make a decision, then see what happens. If I’m wrong, at least I know. Most mistakes aren’t completely irreversible.

That’s how you learn. By fucking up. Trying to fix it. I’ve done plenty of that. The only things I’ve ever really worried about — time, money, and physical harm.

I’ve always tried to give serious thought to any decision that might get my fingers blown off. Or burn my house down. For example, I’m not a big fan of amateur fireworks.

I think I can live a meaningful life without them. Also, I think I can take a pass on climbing Mount Everest.

You can always take steps to minimize your risk. Follow your dreams, but form a backup plan or two. Quit your job, but after you’ve saved up some cash and formed a plan for your alleged startup. Climb a mountain, but train for it. Eat the tide pod, but do it in the ER waiting room.

On a more serious note, don’t eat the tide pod. That’s an example of a senseless risk. And yet…I can’t finish this sentence…because just the thought of eating tide pods makes me facepalm.

Taking risks doesn’t make you cool. It won’t improve your life automatically. Risk just comes with the package. A necessary evil.

Start with Australia

Fortune doesn’t favor the bold. It favors the smart. Not many people wing their entire life. They plan. Strategize. They don’t risk everything all the time. They decide what to risk and when.

The odds don’t have to stand in your favor. But they should beat a million to one.

That’s why you always start with Australia. Be honest, you’ve been waiting the entire post for this analogy.

Only two men per turn. Sounds pathetic. And yet that quiet opponent almost always wins. Sure, they took risks. They also exercised caution, patience, and sound judgment.

Even if they don’t win, they always last longer than the dumbass who tries to hold all of Asia.

Life goes the same way. Start small. Build momentum. Take medium risks. Most big risks come from the wrong place. Overconfidence. Desperation. Too much caffeine. You always have to balance risk with caution. Do that and you can conquer the world, one turn at a time.